3,3-Dimethylbutane-2-ol

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Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil393. ± 2.KAVGN/AAverage of 21 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple278.4KN/AZubkov, Peshenko, et al., 1990Uncertainty assigned by TRC = 0.15 K; TRC
Quantity Value Units Method Reference Comment
Δvap53.8 ± 0.3kJ/molGSKulikov, Verevkin, et al., 2001Based on data from 280. to 315. K.; AC

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
48.3317.AStephenson and Malanowski, 1987Based on data from 302. to 401. K.; AC
46.8353.N/AWilhoit and Zwolinski, 1973Based on data from 338. to 393. K.; AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C6H13O- + Hydrogen cation = 3,3-Dimethylbutane-2-ol

By formula: C6H13O- + H+ = C6H14O

Quantity Value Units Method Reference Comment
Δr1556. ± 8.4kJ/molD-EAMihalick, Gatev, et al., 1996gas phase; Derived BDE: 103.3±2.8 kcal/mol; B
Δr1554. ± 8.4kJ/molCIDCHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B
Δr1553. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1528. ± 8.4kJ/molIMREClifford, Wenthold, et al., 1998gas phase; B
Δr1528. ± 8.8kJ/molH-TSMihalick, Gatev, et al., 1996gas phase; Derived BDE: 103.3±2.8 kcal/mol; B
Δr1526. ± 8.8kJ/molH-TSHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B
Δr1525. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

C7H7O- + 3,3-Dimethylbutane-2-ol = (C7H7O- • 3,3-Dimethylbutane-2-ol)

By formula: C7H7O- + C6H14O = (C7H7O- • C6H14O)

Quantity Value Units Method Reference Comment
Δr120. ± 12.kJ/molN/ACaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M
Quantity Value Units Method Reference Comment
Δr123.J/mol*KN/ACaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Δr83.7 ± 8.4kJ/molIMRECaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M

C6H13O- + 3,3-Dimethylbutane-2-ol = (C6H13O- • 3,3-Dimethylbutane-2-ol)

By formula: C6H13O- + C6H14O = (C6H13O- • C6H14O)

Quantity Value Units Method Reference Comment
Δr120.kJ/molICRCaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Δr123.J/mol*KN/ACaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Δr83.3kJ/molICRCaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M

C6H13O- + 3,3-Dimethylbutane-2-ol = (C6H13O- • 3,3-Dimethylbutane-2-ol)

By formula: C6H13O- + C6H14O = (C6H13O- • C6H14O)

Quantity Value Units Method Reference Comment
Δr121. ± 12.kJ/molN/ACaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr82.8 ± 8.4kJ/molIMRECaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B

Fluorine anion + 3,3-Dimethylbutane-2-ol = (Fluorine anion • 3,3-Dimethylbutane-2-ol)

By formula: F- + C6H14O = (F- • C6H14O)

Quantity Value Units Method Reference Comment
Δr146.0kJ/molN/AMihalick, Gatev, et al., 1996gas phase; affinity derived using a ROH..F. neutral binding energy of 10.3 kcal/mol.; B

Gas phase ion energetics data

Go To: Top, Phase change data, Reaction thermochemistry data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H5O+10.14(CH3)3CEIHolmes, Lossing, et al., 1988LL
C2H5O+10.12 ± 0.05tert-C4H9EIHolmes and Lossing, 1984LBLHLM

De-protonation reactions

C6H13O- + Hydrogen cation = 3,3-Dimethylbutane-2-ol

By formula: C6H13O- + H+ = C6H14O

Quantity Value Units Method Reference Comment
Δr1556. ± 8.4kJ/molD-EAMihalick, Gatev, et al., 1996gas phase; Derived BDE: 103.3±2.8 kcal/mol; B
Δr1554. ± 8.4kJ/molCIDCHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B
Δr1553. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1528. ± 8.4kJ/molIMREClifford, Wenthold, et al., 1998gas phase; B
Δr1528. ± 8.8kJ/molH-TSMihalick, Gatev, et al., 1996gas phase; Derived BDE: 103.3±2.8 kcal/mol; B
Δr1526. ± 8.8kJ/molH-TSHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B
Δr1525. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

Ion clustering data

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C6H13O- + 3,3-Dimethylbutane-2-ol = (C6H13O- • 3,3-Dimethylbutane-2-ol)

By formula: C6H13O- + C6H14O = (C6H13O- • C6H14O)

Quantity Value Units Method Reference Comment
Δr121. ± 12.kJ/molN/ACaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr82.8 ± 8.4kJ/molIMRECaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B

C6H13O- + 3,3-Dimethylbutane-2-ol = (C6H13O- • 3,3-Dimethylbutane-2-ol)

By formula: C6H13O- + C6H14O = (C6H13O- • C6H14O)

Quantity Value Units Method Reference Comment
Δr120.kJ/molICRCaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Δr123.J/mol*KN/ACaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Δr83.3kJ/molICRCaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M

C7H7O- + 3,3-Dimethylbutane-2-ol = (C7H7O- • 3,3-Dimethylbutane-2-ol)

By formula: C7H7O- + C6H14O = (C7H7O- • C6H14O)

Quantity Value Units Method Reference Comment
Δr120. ± 12.kJ/molN/ACaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M
Quantity Value Units Method Reference Comment
Δr123.J/mol*KN/ACaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Δr83.7 ± 8.4kJ/molIMRECaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M

Fluorine anion + 3,3-Dimethylbutane-2-ol = (Fluorine anion • 3,3-Dimethylbutane-2-ol)

By formula: F- + C6H14O = (F- • C6H14O)

Quantity Value Units Method Reference Comment
Δr146.0kJ/molN/AMihalick, Gatev, et al., 1996gas phase; affinity derived using a ROH..F. neutral binding energy of 10.3 kcal/mol.; B

IR Spectrum

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

Data compiled by: Tanya L. Myers, Russell G. Tonkyn, Ashley M. Oeck, Tyler O. Danby, John S. Loring, Matthew S. Taubman, Stephen W. Sharpe, Jerome C. Birnbaum, and Timothy J. Johnson

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin TEXAS A&M UNIVERSITY, COLLEGE STATION, TEXAS, USA
NIST MS number 1163

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


Gas Chromatography

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryMethyl Silicone100.722.Huber, Kenndler, et al., 1993H2; Column length: 5. m; Phase thickness: 2.65 μm
CapillaryMethyl Silicone120.721.Huber, Kenndler, et al., 1993H2; Column length: 5. m; Phase thickness: 2.65 μm
CapillaryMethyl Silicone80.723.Huber, Kenndler, et al., 1993H2; Column length: 5. m; Phase thickness: 2.65 μm
CapillaryOV-10180.722.3Boneva, 1987N2; Column length: 100. m; Column diameter: 0.27 mm
CapillaryOV-10190.723.4Boneva, 1987N2; Column length: 100. m; Column diameter: 0.27 mm
PackedApiezon L120.717.Bogoslovsky, Anvaer, et al., 1978Celite 545
PackedApiezon L160.728.Bogoslovsky, Anvaer, et al., 1978Celite 545

Kovats' RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryPEG-20M110.1114.Huber, Kenndler, et al., 1993Column length: 10. m; Phase thickness: 1.33 μm
CapillaryPEG-20M90.1118.Huber, Kenndler, et al., 1993Column length: 10. m; Phase thickness: 1.33 μm
CapillaryPEG-20M130.1109.1Huber, Kenndler, et al., 1993Column length: 10. m; Phase thickness: 1.33 μm
CapillaryCarbowax 20M80.1112.Boneva, 1987N2; Column length: 50. m; Column diameter: 0.23 mm
CapillaryCarbowax 20M90.1114.Boneva, 1987N2; Column length: 50. m; Column diameter: 0.23 mm

Van Den Dool and Kratz RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryVF-5MS740.6Tret'yakov, 200730. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxanes712.Zenkevich, 1998Program: not specified

References

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Zubkov, Peshenko, et al., 1990
Zubkov, V.I.; Peshenko, A.D.; Markovnik, V.S., Thermodynamic properties of 3-methyl-2-butanol and 3,3-dimethyl-2-butanol in Vses. Konf. Term. Org. Soedin. 6th, Minsk, p 46, 1990. [all data]

Kulikov, Verevkin, et al., 2001
Kulikov, Dmitry; Verevkin, Sergey P.; Heintz, Andreas, Determination of Vapor Pressures and Vaporization Enthalpies of the Aliphatic Branched C 5 and C 6 Alcohols, J. Chem. Eng. Data, 2001, 46, 6, 1593-1600, https://doi.org/10.1021/je010187p . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Wilhoit and Zwolinski, 1973
Wilhoit, R.C.; Zwolinski, B.J., Physical and thermodynamic properties of aliphatic alcohols, J. Phys. Chem. Ref. Data Suppl., 1973, 1, 2, 1. [all data]

Mihalick, Gatev, et al., 1996
Mihalick, J.E.; Gatev, G.G.; Brauman, J.I., Electron Photodetachment Spectroscopy of Solvated Anions: RO.HF- or ROH.F-?, J. Am. Chem. Soc., 1996, 118, 49, 12424, https://doi.org/10.1021/ja954202k . [all data]

Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G., The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols, Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W . [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Clifford, Wenthold, et al., 1998
Clifford, E.P.; Wenthold, P.G.; Gareyev, R.; Lineberger, W.C.; DePuy, C.H.; Bierbaum, V.M.; Ellison, G.B., Photoelectron spectroscopy, gas phase acidity, and thermochemistry of tert-butyl hydroperoxide: Mechanisms for the rearrangement of peroxyl radicals, J. Chem. Phys., 1998, 109, 23, 10293-10310, https://doi.org/10.1063/1.477725 . [all data]

Caldwell, Rozeboom, et al., 1984
Caldwell, G.; Rozeboom, M.D.; Kiplinger, J.P.; Bartmess, J.E., Anion-alcohol hydrogen bond strengths in the gas phase, J. Am. Chem. Soc., 1984, 106, 4660. [all data]

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Thermodynamics of the Association Reactions OH- - H2O = HOHOH- and CH3O- - CH3OH = CH3OHOCH3- in the Gas Phase, J. Phys. Chem., 1990, 94, 12, 5184, https://doi.org/10.1021/j100375a076 . [all data]

Meot-ner and Sieck, 1986
Meot-ner, M.; Sieck, L.W., Relative acidities of water and methanol, and the stabilities of the dimer adducts, J. Phys. Chem., 1986, 90, 6687. [all data]

Meot-Ner(Mautner), 1986
Meot-Ner(Mautner), M., Comparative Stabilities of Cationic and Anionic Hydrogen-Bonded Networks. Mixed Clusters of Water-Methanol, J. Am. Chem. Soc., 1986, 108, 20, 6189, https://doi.org/10.1021/ja00280a014 . [all data]

Holmes, Lossing, et al., 1988
Holmes, J.L.; Lossing, F.P.; Maccoll, A., Heats of formation of alkyl radicals from appearance energies, J. Am. Chem. Soc., 1988, 110, 7339. [all data]

Holmes and Lossing, 1984
Holmes, J.L.; Lossing, F.P., Heats of formation of organic radicals from appearance energies, Int. J. Mass Spectrom. Ion Processes, 1984, 58, 113. [all data]

Huber, Kenndler, et al., 1993
Huber, J.F.K.; Kenndler, E.; Reich, G.; Hack, W.; Wolf, J., Optimal Selection of Gas Chromatographic Columns for the Analytical Control of Chemical Warfare Agents by Application of Information Theory to Retention Data, Anal. Chem., 1993, 65, 20, 2903-2906, https://doi.org/10.1021/ac00068a031 . [all data]

Boneva, 1987
Boneva, S., Gas Chromatographic Retention Indices for C6 Alkanols on OV-101 and Carbowax 20M Capillary Columns, Chromatographia, 1987, 23, 1, 50-52, https://doi.org/10.1007/BF02310419 . [all data]

Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

Tret'yakov, 2007
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]

Zenkevich, 1998
Zenkevich, I.G., The Principle of Structural Analogy in the Calculation of Gas Chromatographic Retention Indices using Physico-Chemical Constants of Organic Compounds, Zh. Anal. Khim. (Rus.), 1998, 53, 1, 43-49. [all data]


Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References